I drive every time it's more convenient to take a car than to walk/bike/transit. Usually works out to once a week at most. I only have a car because I used to work in the suburbs. Between insurance, maintenance, tire swaps and storage, etc. it costs me at least $50 for every time I take it out, probably more.
I feel the same way at times. Were it not for aged parents in outer surburbia, and other family in rural Quebec, I'd ditch my car happily.
Still the claim that one frequently ends up spending $60 on Uber is just silly. I always use cabs, and that's a VERY long cab ride - and my understanding is that Uber is significantly cheaper.
And in my 20-years in Toronto, which have included many years of taking transit every day, I've only once ever given up on the TTC, and switched to car. (in this case I was, after 45-minutes, still a 15-minute walk from home, so I walked back and got my car).
Sure, there's been the occasional really excessively long trip. But some of the car trips have been just whacky too, taking half-an-hour to go one traffic light.
And yes, for some trips, transit doesn't work. Normally when carrying cargo of some time. In fact, I'm just jumping into the car, to drive to near the Zoo to pick up two cats that were being boarded. That wouldn't work well on transit. It would have been a great carshare trip though.